Aniline → HCID 18003168, compound

HRID 1355312Notes

Reaction equation

HRID 1355312 reaction equation
[C:1]1(=O)[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:12]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH2:15])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

3

Reactant 2

HCID 6115AnilineHCID 22281833Fluoreneone

Product 1

HCID 18003168HCID 18003168, compound

Procedure

More specifically, a symmetrical compound can be synthesized by the following method: A mixture containing a fluorenone and an aniline is refluxed in the presence of an acid catalyst to produce an intermediate 9,9-bis(aminophenyl)fluorene. The intermediate is subsequently reacted with aryl halides (Ar—X and Ar′—X, stepwise) in the presence of a catalyst such as palladium to obtain the desired symmetrical product. An asymmetrical compound, on the other hand, can be synthesized as follows: A reaction mixture containing a fluorenone and two different anilines (e.g., an aniline and a 2-fluoroaniline as shown in the above scheme) is refluxed in the presence an acid catalyst to produce a mixture including an asymmetric fluorene intermediate. The asymmetric fluorene intermediate is then reacted with aryl halides (Ar—X and Ar′—X, stepwise) in the presence of a catalyst such as palladium to produce the desired asymmetrical product.

Workup

  1. customMore specifically, a symmetrical compound can be synthesized by the following method

Sources & evidence

ORD record
ord-08fa2bae686b4379b99b71a170987bdf
Source dataset
uspto-grants-2003_07
Patent number
US06586120B2

Reaction notes

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